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膦催化的硝基亚乙烯和烯酮的形式[4 + 2]环加成反应:二氢吡喃的对映选择性合成。

Phosphine-Catalyzed Formal Oxa-[4 + 2] Annulation Employing Nitroethylene and Enones: Enantioselective Synthesis of Dihydropyrans.

机构信息

Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543 , Singapore.

National University of Singapore (Suzhou) Research Institute , 377 Lin Quan Street, Suzhou Industrial Park , Suzhou , Jiangsu 215123 , PR China.

出版信息

Org Lett. 2018 Sep 7;20(17):5515-5518. doi: 10.1021/acs.orglett.8b02519. Epub 2018 Aug 22.

DOI:10.1021/acs.orglett.8b02519
PMID:30133289
Abstract

The first phosphine-catalyzed enantioselective formal oxa-[4 + 2] reaction between nitroethylene and α-cyano-α,β-unsaturated ketones has been developed. In the presence of a dipeptide-based phosphine catalyst and achiral Brønsted acid additives, highly functionalized 3,4-dihydro-2 H-pyrans were obtained with excellent enantio- and diastereoselectivities.

摘要

首次发展了膦催化的硝基乙烯与α-氰基-α,β-不饱和酮的对映选择性形式氧杂-[4 + 2]反应。在二肽基膦催化剂和手性 Brønsted 酸添加剂的存在下,高官能化的 3,4-二氢-2H-吡喃以优异的对映选择性和非对映选择性得到。

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